Prediction of Thermal Isomerization Temperatures of Substituted Benzocyclobutenes to o-Quinodimethanes by Semi-Empirical Molecular Orbital Calculation

Author(s): Keisuke Chino, Takeshi Endo.

Journal Name: Letters in Organic Chemistry

Volume 8 , Issue 2 , 2011

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Abstract:

Bezocyclobutenes are useful compounds as precursors to o-quinodimethanes, which are highly reactive dienes. However, the thermal isomerization temperatures(IT) of substituted benzocyclobutenes to o-quinodimethanes have not been predictable based on the simple substituent effect. In this paper, we provide a simple method to predict the IT of benzocyclobutenes by calculation of the activation energies using a semi-empirical molecular orbital calculation. ITs of the various substituted benzocyclobutenes were estimated by this method.

Keywords: Bezocyclobutene, o-quinodimethane, thermal isomerization temperature, prediction, activation energy, semiempirical molecular orbital calculation, captodative effect, aminomethane, Diels-Alder reaction, cyanobenzocyclobutene

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Article Details

VOLUME: 8
ISSUE: 2
Year: 2011
Page: [138 - 142]
Pages: 5
DOI: 10.2174/157017811794697539
Price: $58

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